2-bromo-1-phenyl-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】44573

【品名】2-bromo-1-phenyl-1-ethanone

【CA登记号】

【分子式】C₈H₇BrO

【分子量】199.04698

【元素组成】C 48.27% H 3.54% Br 40.14% O 8.04%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

The bromination of labeled acetophenone (I) with Br2 and AlCl3 gives phenacyl bromide (II), which is condensed with N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylamine (III), yielding the 2-aminoacetophenone (IV). The reduction of (IV) with NaBH4 affords the secondary alcohol (V), which is finally cyclized by means of H2SO4 and trifluoroacetic acid to provide the target 3-benzazepine.

参考文献中间体

合成目标

【1】 Hieble, J.P.; Wilson III, J.W.; Weinstock, J.; The chemistry and pharmacology of 3-benzazepines derivatives. Drugs Fut 1985, 10, 8, 645.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	10317	Acetophenone	98-86-2	C₈H₈O	详情	详情
(I)	44572	acetophenone		C₈H₈O	详情	详情
(II)	10315	2-Bromo-1-phenyl-ethanone; 2-Bromo-1-phenyl-1-ethanone	70-11-1	C₈H₇BrO	详情	详情
(II)	44573	2-bromo-1-phenyl-1-ethanone		C₈H₇BrO	详情	详情
(III)	18938	2-(3,4-dimethoxyphenyl)-N-methyl-1-ethanamine; N-(3,4-dimethoxyphenethyl)-N-methylamine	3490-06-0	C₁₁H₁₇NO₂	详情	详情
(IV)	44047	2-[(3,4-dimethoxyphenethyl)(methyl)amino]-1-phenyl-1-ethanone		C₁₉H₂₃NO₃	详情	详情
(IV)	44574	2-[(3,4-dimethoxyphenethyl)(methyl)amino]-1-phenyl-1-ethanone		C₁₉H₂₃NO₃	详情	详情
(V)	44048	2-[(3,4-dimethoxyphenethyl)(methyl)amino]-1-phenyl-1-ethanol		C₁₉H₂₅NO₃	详情	详情
(V)	44575	2-[(3,4-dimethoxyphenethyl)(methyl)amino]-1-phenyl-1-ethanol		C₁₉H₂₅NO₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The bromination of labeled acetophenone (I) with Br2 and AlCl3 gives the phenacyl bromide (II), which is reduced with NaBH4, yielding 2-bromo-1-phenylethanol (III). The condensation of (III) with N-benzyl-N-[2-(3,4-dimethoxyphenyl)ethyl]amine (IV) affords the tertiary amine (V), which is debenzylated by hydrogenolysis with H2 over Pd/C to provide the substituted ethanolamine (VI). Finally, this compound is cyclized and demethylated by treatment with 48% HBr to provide the target benzazepine.

参考文献中间体

合成目标

【1】 Hieble, J.P.; Wilson III, J.W.; Weinstock, J.; The chemistry and pharmacology of 3-benzazepines derivatives. Drugs Fut 1985, 10, 8, 645.
【2】 Bass, L.S.; Dandridge, P.A.; Setler, P.E.; Sarau, H.M.; Garvey, E.; Clardy, J.; Hanhn, R.A.; Kaiser, C.; Absolute stereochemistry and dopaminergic activity of enantiomers of 2,3,4,5-tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine. J Med Chem 1982, 25, 6, 697-703.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	10317	Acetophenone	98-86-2	C₈H₈O	详情	详情
(I)	44572	acetophenone		C₈H₈O	详情	详情
(II)	10315	2-Bromo-1-phenyl-ethanone; 2-Bromo-1-phenyl-1-ethanone	70-11-1	C₈H₇BrO	详情	详情
(II)	44573	2-bromo-1-phenyl-1-ethanone		C₈H₇BrO	详情	详情
(III)	44060	2-bromo-1-phenyl-1-ethanol		C₈H₉BrO	详情	详情
(III)	44632	2-bromo-1-phenyl-1-ethanol		C₈H₉BrO	详情	详情
(IV)	44061	N-benzyl-2-(3,4-dimethoxyphenyl)-1-ethanamine; N-benzyl-N-(3,4-dimethoxyphenethyl)amine		C₁₇H₂₁NO₂	详情	详情
(V)	44062	2-[benzyl(3,4-dimethoxyphenethyl)amino]-1-phenyl-1-ethanol		C₂₅H₂₉NO₃	详情	详情
(V)	44633	2-[benzyl(3,4-dimethoxyphenethyl)amino]-1-phenyl-1-ethanol		C₂₅H₂₉NO₃	详情	详情
(VI)	39206	2-[(3,4-dimethoxyphenethyl)amino]-1-phenyl-1-ethanol		C₁₈H₂₃NO₃	详情	详情
(VI)	44634	2-[(3,4-dimethoxyphenethyl)amino]-1-phenyl-1-ethanol		C₁₈H₂₃NO₃	详情	详情

Extended Information